Sulfadoxine

Basic Info

Common NameSulfadoxine(F05885)
2D Structure
FRCD IDF05885
CAS Number2447-57-6
PubChem CID17134
FormulaC12H14N4O4S
IUPAC Name

4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide

InChI Key

PJSFRIWCGOHTNF-UHFFFAOYSA-N

InChI

InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

Canonical SMILES

COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N

Isomeric SMILES

COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N

Synonyms
        
            Sulforthomidine
        
            4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
        
            SULFADOXINE
        
            2447-57-6
        
            Sulphadoxine
        
            Fanasil
        
            Sulphormethoxine
        
            Sulfadoxin
        
            Sulfadoxina
        
            Sulfadoxinum
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzenesulfonamides
Intermediate Tree NodesNot available
Direct ParentAminobenzenesulfonamides
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsAminobenzenesulfonamide - Benzenesulfonyl group - Aniline or substituted anilines - Alkyl aryl ether - Pyrimidine - Organosulfonic acid amide - Imidolactam - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Heteroaromatic compound - Organoheterocyclic compound - Ether - Azacycle - Organic oxygen compound - Organic oxide - Amine - Organic nitrogen compound - Organopnictogen compound - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Properties

Property NameProperty Value
Molecular Weight310.328
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Complexity420
Monoisotopic Mass310.074
Exact Mass310.074
XLogP0.7
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.5345
Human Intestinal AbsorptionHIA+0.9602
Caco-2 PermeabilityCaco2-0.5900
P-glycoprotein SubstrateNon-substrate0.8126
P-glycoprotein InhibitorNon-inhibitor0.8320
Non-inhibitor0.8892
Renal Organic Cation TransporterNon-inhibitor0.9164
Distribution
Subcellular localizationMitochondria0.4890
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6930
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.6464
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.8703
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6052
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9907
Non-inhibitor0.7221
AMES ToxicityNon AMES toxic0.6456
CarcinogensNon-carcinogens0.8265
Fish ToxicityLow FHMT0.8230
Tetrahymena Pyriformis ToxicityLow TPT0.6400
Honey Bee ToxicityLow HBT0.8331
BiodegradationNot ready biodegradable0.9960
Acute Oral ToxicityIII0.5764
Carcinogenicity (Three-class)Non-required0.5473
Model Value Unit
Absorption
Aqueous solubility-2.8846LogS
Caco-2 Permeability0.7364LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8756LD50, mol/kg
Fish Toxicity1.7442pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2564pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.06ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Pig,Edible OffalJapan0.02ppm
Cattle,Edible OffalJapan0.1ppm
Other Terrestrial Mammals,KidneyJapan0.1ppm
Pig,KidneyJapan0.1ppm
Cattle,KidneyJapan0.1ppm
Other Terrestrial Mammals,LiverJapan0.1ppm
Pig,LiverJapan0.1ppm
Cattle,LiverJapan0.1ppm
Other Terrestrial Mammals,FatJapan0.1ppm
Pig,FatJapan0.1ppm
Cattle,FatJapan0.1ppm
Other Terrestrial Mammals,MuscleJapan0.1ppm
Pig,MuscleJapan0.1ppm
Cattle,MuscleJapan0.1ppm

References

TitleJournalDatePubmed ID
Correlation between drug-drug interaction-induced Stevens-Johnson syndrome and related deaths in Taiwan.J Food Drug Anal2016 Apr28911598
Fabrication of CoFe2O4-graphene nanocomposite and its application in the magneticsolid phase extraction of sulfonamides from milk samples.Talanta2015 Nov 126452959
Development of a high performance liquid chromatography method and a liquidchromatography-tandem mass spectrometry method with the pressurized liquidextraction for the quantification and confirmation of sulfonamides in the foodsof animal origin.J Chromatogr B Analyt Technol Biomed Life Sci2011 Sep 121840270
Occurrence of veterinary antibiotics in animal wastewater and surface wateraround farms in Jiangsu Province, China.Chemosphere2011 Mar21159362
Determination of sulfonamide residues in the tissues of food animals usingautomated precolumn derivatization and liquid chromatography with fluorescencedetection.J AOAC Int2004 Sep-Oct15493686
Absorption of two trimethoprim/sulphonamide combinations from the uterus of pony mares.J Vet Pharmacol Ther1989 Dec2614860